Manufacture of lubricating greases by alkali fusion of ether alcohols



United States Patent 2,801,972 MANUFACTURE OF LUBRICATING GREASES BY ALKALI FUSION OF ETHER ALCOHQ'LS Jeffrey H. Bartlett, Westiield, Arnold J. Morway, Rah way, and Louis A. .Mikeska, Westfield, N. J., *assignor's to Esso Research and Engineering Company, a corpo ration of Delaware No Drawing. Application December 1, 1952, Serial No. 323,512 11 Claims. (Cl. 252-41) The present invention relates to an improved method of preparing lubricating greases and to grease compositions produced by this method. More specifically, the invention pertains .to improvements in the manufacture of grease thickeners and to greases containing such thickeners. In its broadest aspect, the invention provides an improved method of preparing ether acids and grease thickeners by fusing high molecular weight ether derivatives havinga primary alcohol group with caustic alkali, producing a metal soap from the ether acid so formed and incorporating this metal soap into alubricating oil in grease making proportions. In a preferred embodiment of the invention, the fusion is carried out in the presence of lubricating oil.

Lubricating greases normally consist of lubricating oils thickened by alkali and alkaline earth metal soaps or other thickeners to a solid or semisolid consistency. The soaps may be prepared by the neutralization of high molecular weight fatty acids or by the saponification of fats which is usually carried out in a portion of the oil to be thickened. Saponification of fats has been the preferred grease making method heretofore chiefly because greases produced in the absence of glycerineor similar materials have tendencies to become crumbly, to sweat oil and to break down into soft granular masses of reduced lubricating value. More recently, fatty acids are being frequently employed in combinationwith the glycerides for various purposes, such as improvements in structure of the grease, its high temperature characteristics, etc. i

The present invention pertains 'ot highly valuable, stable lubricating greases in which the high molecular Weight fatty acids are replaced or at least supplemented by a new grease making material. It has now been found that such greases may be prepared by incorporating into lubricating oils a grease thickener obtained by fusing high molecular weight ether derivativeshaving a primary alcohol group, with alkali, particularly caustic soda or potash at temperatures of about 400-620 F., preferably about 500575 F. for a time sufficient to form the alkali metal salt of the acid corresponding to the ether-alcohol used. The c'hemicalreaction taking place during the fu sion process may be illustrated by the following equation:

wherein B may be an ether radical containing 10 or more carbon atoms and M is an alkali metal, such as sodium or potassium. i

The discovery of the utility of alkali fusion of high molecular weight ether alcohols for grease making greatly increases the wealth of raw materials available for grease production. Heretofore, ester-type fats, oils or high mo lecular weight fatty acids have been used exclusively in the manufacture of soap-thickened greases and these starting materials have been believed indispensable for the purpose. All these materials have numerous other industrial uses, a situation conducive to the development of shortages forcing undesirable variations in grease making procedures and grease characteristics. The discovery of an entirely new and large class of suitable raw materials eases this situation considerably. 7

Three factors further contribute to the value of high molecular weight ether alcohols as grease making materials. In the first place, their use introduces no complication into the grease making procedure. While alkali fusion of the ether alcohol may be carried out in a separate preliminary acid-forming stage, the greases are preferably produced essentially in a single process step in which the high molecular Weight ether alcohol is fused with alkali in the lubricating oil base in grease making proportions and at grease making conditions, although at some what higher temperatures. At the conclusion of the fusion process a finished grease is obtained.

Secondly, no water is formed during the reaction so that no excessive foaming occurs. Slight foaming caused by the evolution of hydrogen is not a great inconvenience.

Finally, ether alcohols useful for the purposes of the present invention may be prepared on the basis of primary alcohols which have become available in large quantities as intermediate or final products of various synthesis processes and more particularly as products and by-products of the well-known Oxo synthesis. The last-named process involves the catalytic reaction of olefins with carbon monoxide and hydrogen at elevated temperatures, :say about 300400 F., and pressures of about 2500-4000 p. s. i. g. in the presence of group VIII metal catalysts, particularly cobalt catalysts, to form saturated .aldehydes having one carbon atom more than the olefin originally used. The aldehyde is catalytically hydrogenated to the corresponding alcohol which is recoveredrby distillation from the reaction mixture leaving the so-called Oxo-bottoms, consisting of higher boiling materials rich in alcohols. The present invention is applicable to high molecular weight alcohols so prepared and recovered overhead from the distillation stage. However, a highly desirable embodiment of the invention involves the use of the Oxo bottoms as such in the production of starting materials for the new grease making process.

Quite generally, ether alcohols may be used which have about 10-50 or more carbon atoms per molecule and a suificiently high boiling point to prevent excessive volatilization during the fusion process. The ether alcohols suitable for the invention have the general formula RX(CHCH -O),,OHOH2OH p and yield upon alkali fusion ether acids of the formula R-X(o1aoH.o .cH000H wherein X=oxygen or sulfur R=a hydrocarbon group containing from 1-40 carbon atoms selected from the group consisting of alkyl, alkylene, naphthenyl, aryl alkaryl and aralkyl y: an integer from 1-50 These ether alcohols include the straight chain or branched chain alkyl or arylmonoethers or thioethers of alkylene or polyalkylene (e. g. ethylene, propylene, polyethylene, polypropylene) glycols. Specific examples of these compounds are normal butyl monoether of tetradecapropylene glycol "-040 (OH'CH2-O)14H H; non'yl phenyl monoether of decaethylene glyol 3 decyl monoether of diethylene glycol C1oO(CH2CH2O)2I-I; tridecyl monoether of diethylene glycol C130(CH2CH20)2H hexadecyl monoether of diethylene glycol C160 (CHzCHzO 2H octadecyl monoether of diethylene glycol C130(CH2CH20)2H octadecyl monoether of pentaoontaethylene glycol C1aO(CH2CH2O)5bH octadecyl monoether of pentacontapropylene glycol om(oH0HzO)4poHoH,-0H

(1H3 5H3 octadecyl monoether of dodecaalkylene glycol C1s(OCH-CH2)12OH it octadecyl monoether of dodecaethylene dodecapropylene glycol C150 (CHgCHrO)u(CHCHz-O)12H decyl-, dodecyl-, tridecyl-, tetradecyl-, etc. monoethers of deca-, dodeca-, eicosa-, heneicosa-, docosa-, triaconta-, tetraconta-, pentaconta-ethylene or -propylene glycols; the corresponding monothioethers, such as the decyl-, dodecyl-, tridecyl-, octodecyl-, etc. monothioethers of diethylene or polyethylene glycols C '18S(cH2cH20)2'-50H; etc.

Particularly desirable starting materials are the ether alcohols obtained from branched chain primary alcohols, such as those obtained from isodecyl, tridecyl, hexadecyl alcohols and similar alcohols formed by oxonation of polymerized olefins or olefins from cracked waxes, cracked petrolatums and other high molecular weight hydrocarbon products, for example Fischer-Tropsch olefins.

When using Oxo-bottoms in accordance with one of the embodiments of the invention, the distillation residue of the hydrogenated oxonation product of a wide variety of oxonation reactions may be used. Quite generally, the distillation bottoms obtained in the successive oxonation, hydrogenation and distillation of mono-olefins having 3-25 carbon atoms or more per molecule are preferred for the purposes of the invention.

Other starting materials for the preparation of ether alcohols suitable for the purposes of the invention include hydroxy or mercapto compounds of the type of primary aliphatic alcohols, such as propyl, butyl, hexyl, isooctyl, 2-ethyl hexyl, decyl, tridecyl, stearyl, wax alcohols, cyclohexanol and similar alcohols; substituted or unsubstituted phenols or naphthols, particularly alkylated phenols, such as isooctyl phenol, cresols, petroleum phenols, polyalkyl ated phenols, Wax-alkylated phenols, cardanol, di-iso-octyl phenol, nonyl phenol, etc.; mercaptans, such as octadecyl mercaptan, tertiary dodecyl mercaptan; and other thiols corresponding to the hydroxy compounds disclosed above.

The ether alcohols to be subjected to alkali fusion in accordance with the invention may be prepared from these starting materials quite generally by a reaction with alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, nonylene oxide, hexadecene oxide, butadiene monoxide, styrene monoxide, etc. at temperatures of about 0-100" C. in the presence of alkaline or acid catalysts, for example a boron fluoride-type catalyst to form monoglycol or polyglycol ethers having at least one primary alcohol group. The amount of alkylene oxide used may be as high as 50 or more mols for each mol of the hydroxy or thiol compound used as the starting material.

The water and oil solubility of this end product may be controlled to a certain degree by a proper choice of the molecular weight of the alkylene oxide used. In general, the higher the molecular weight of the alkylene oxide the lower the water solubility and the higher the oil solubility of the end product. Thus, water insoluble, oil soluble end products may be produced by combining the low molecular weight hydroxy compounds with high molecular weight alkylene oxides.

The reactions involved inthe formation of suitable ether alcohols from hydroxy or thiol compounds and alkylene oxides may be illustrated by the following equations:

The ether alcohols produced in this manner may then be converted into the corresponding carboxylic acids or their soaps by fusion with alkali as described above and illustrated with reference to Equation 1. While the acids and soaps may be produced in a separate process step and the preformed products incorporated into lubricating oils in grease making proportions, a particular advantage of the present invention resides in the fact'that the new grease thickeners may be prepared in situ in the lubricating oil as an integral stage of the grease making process. In other words, the ether alcohols may be. converted into soaps by alkali fusion in the grease kettle using the lubri eating oil base of the grease as a reaction medium.

When carrying out this preferred embodiment of the invention, it has been observed that the alkali has a strong tendency to settle out of the reaction mixture to the bottom of the reactor in the form of a cake which does not fully participate in the reaction. Highly efficient stirring or agitation will counteract this tendency. However, in many cases more efiicient stirring is required than may be obtained in conventional grease kettles and special equipment is necessary.

I This settling tendency of the alkali in the lubricating oil-ether alcohol mixture is negligible when a sufiicient amount of a solid suspending agent is present in the re action mixture. Most desirable suspending agents are those which serve simultaneously as grease thickeners, such as soaps of high molecular weight fatty acids, silica gel, carbon black, bentones, Attapulgus clay modifications, etc. Soaps, particularly sodium soaps of high molecular weight fatty acids, are preferred for this purpose. However, the melting points of most of these soaps in lubricating oil is rather low, usually below 400 F. Thus, at the high reaction or fusion temperature of about 500 F. or thereabove, these soaps are liquid when used as such and do not entirely counteract the settling tendency of the alkali. This difiiculty may be overcome in accordance with a specific embodiment of the invention by using the salt, preferably the alkali metal salt, ofv a low molecular Weight acid in addition to the high molecular weight fatty acid soap. In this manner, soap-salt complexes are formed which melt well above 500 F. and thus form an excellent suspending agent.

. These soaps or soap-salt complexes are preferably formed in situ by neutralization of the corresponding acids .in the alcohol-oil mixture with alkali added in amounts suflicient for this neutralization and the subsequent fusion which takes place at considerably higher temperatures. High molecular weight acids useful for this purpose include hydrogenated fish oil acids, C12-C22 naturally occurring acids of animal or vegetable origin, etc. These acids may be used in amounts ranging from about 2-30 wt. percent based on the finished product. Suitable low molecular weight acids include acetic, furoic, acrylic and similar acids to be used in proportions of about 1-10 wt. percent based on the finished product. Esters, e. g. glycerides of the high and/ or low molecular weight acids, particularly those containing mono basic acid esters may be used in place of the free acids in corresponding proportions. In this case, the alcohol portions of the esters are converted into acids and the corresponding soaps by alkali fusion. If esters of low molecular weight alcohols are used, elevated pressures may be employed to prevent volatilization of the alcohols. Qf course, esters of non-volatile low molecular weight alcohols, such as. polyhydroxy alcohol esters, tate, etc. may be used. weight type of acids or may also be prepared by alkali fusion of ether alcohols. In this case, ,a portion of the product of the alkali fusion process in which the principal grease thickener is prepared in accordance with the invention may be returned to the fusion stage to serve as an agent preventing settling of the alkali.

Soaps of high molecular weight fatty acids and/or soap-salt complexes of the type specified may be incorporated in the greases of the present invention to improve high temperature or other characteristics even if no suspending agents are required. Thus, it has been found that the use of soaps derived from branched-chain ether alcohols as the sole grease thickeners often tend to form rubbery or cohesive structures which may be undesirable. However, when these branched-chain soaps are mixed with soaps derived from straight-chain fatty acids, this cohesive structure is largely eliminated or modified to an extent that is desirable for certain purposes.

A complex soap thickener of this type may consist of a mixture of high molecular weight soaps of fatty acids and a glycol ether derivative of C Oxo alcohol and Particularly the. high molecular a low molecular weight salt formed from glycerine. In

the formation of a grease, the high molecular weight fatty acid soap portion of the thickener is formed by neutralization of the acidwith sodium hydroxide. The portion of the soap thickener formed from the glycol ether derivative of C10 Oxo alcohol results from a reaction of this ether alcohol with sodium hydroxide to form the sodium soap by fusion and release of hydrogen. At the same time the glycerine is dehydrated to acrolein at the elevated temperatures (above 500 F.) and this acrolein reacts with sodium hydroxide by a Cannizzaro reaction or by direct fusion to form sodium acrylate. All these reactions may be carried out in mineral oil which acts as an inert diluent and finally, on cooling, as the soap dispersant to form the lubricant. The glycerine present may be an added ingredient or it may come in part from a fat used in place of the fatty acid, the glycerine being formed during saponification of the whole fat.

The soaps formed by alkali fusion of ether alcohols in the presence of other fatty acid soaps consistently yield excellent smooth greases. Other conventional thickeners,

antioxidants, corrosion inhibitors, tackiness agents, loadcarrying compounds, viscosity index improvers, oiliness agents, and the like may be added prior, during and/or after the fusion process as will be apparent to those skilled in the art.

The base oil used as menstruum during the fusion process should be a mineral lubricating oil. After the fusion is completed, synthetic lubricating oils, such as a dibasic acid ester (e. g. di-Z-ethyl hexyl sebacate, adipate, etc), polyglycol type synthetic oils, esters of dibasic acids and polyhydric alcohols, etc., as well as alkyl silicates, carbonates, formals, acetals, etc., may be used alone or in addition to mineral lubricating oil to bring the grease to the desired consistency. The oil base preferably comprises about 50 to about 95% of the total weight of the finished grease.

As indicated above, the alkali fusion of the invention e. g. sorbitol acetate, glycol acetheir esters used for this purpose 1 maintained at fusion temperatures of, say, about 400- 620 F. The amount of alkali employed may be substantially stoichiometricor somewhat higher, for example from 1-3 mols of alkali per mol of ether alcohol. When all the ether alcohol has been added, heating may be continued at these temperatures until gas evolution substantially ceases. The acid formed may be recovered from the reaction mixture after cooling, by dilution with water or with 50% isopropanol, followed by extraction of the oil and any unreacted alcohol with a suitable solvent, such as heptane or the like, and acidification of the aqueous rafiinate. If desired, the free acid may be purified by vacuum distillation. The acid so prepared may then be introduced into a lubricating oil base stock, other high and/or low molecular weight fatty acids as well as other grease additives maybe added and the mixture may be converted into a grease by the addition of at least sulficient caustic alkali, preferably in aqueous solution, to neutralize the acids present. Conventional grease-making conditions including temperatures of about 350 500 F. maybe used in this stage. The soap derived from the ether alcohol by alkali fusion should form at least 20 wt.

percent and preferably about 30-50 wt. percent of the the type described above. The proportion of soap derived from ether alcohol to soaps and salts derived from other, acids may be about 1:4 to 4:1 and preferably is about 1:1. t t

In order to prepare a grease by alkali fusion of the ether alcohol in situ in accordance with a more desirable embodiment of the invention, the grease-making procedure may be quite generally as follows. A mineral lubricating oil base is mixed with the ether alcohol and the mixture is heated to about l30-l80 F. The alkali is added preferably in the form of an aqueous solution of about 3050% concentration. The mass is then dehydrated at temperatures of about 300-400 F. for about ature of about 400-620 F. and maintained within this range until gas formation has receded appreciably, which takes place usually after about 1-2 hours. The grease may then be allowed to cool under stirring to about 200- 250 F. at whichlevel further additives may be introduced. Finally,,the grease may be poured into pans to be cooled to room temperature.

A similar procedure is employed when the ether alcohol is subjected to alkali fusion in situ in the presence of suspending agents, such as soaps of high molecular weight fatty acids or complexes of such soaps with salts of low low molecular weight acids in accordance with the preferred embodiment of the invention. In this case, the high molecular weight acids are added to the mineral oil together with the ether alcohol while the low molecular weight acid may be added after the initial heating stage immediately prior to the alkali addition. Thereafter, suf-. ficient caustic alkali to neutralize the acids and convert the ether alcohol to soap is added, preferably in the form of an aqueous solution of about 40-50% and the mixture is heated at a saponification temperature of about 300-400 F. until the acids are converted to soaps and salts and all the water is volatilized. Alkali fusion is then carried out substantially as described above, except that less violent stirring is required.

The invention will be best understood by reference to the following specific examples which represent preferred modifications of the invention. i

Example I Thep'o'lye'thylene glycol ether of C13 OX alcohol'was prepared by adding 1.0 weight percent of BF3 to the alcohol and introducing ethylene oxide at 80-100 F. until about 3 mols per mol of alcohol had reacted. The product was treated with sodium carbonate to remove BFa and was then filtered and distilled at reduced pressure. After distillation of unreacted alcohol, an overhead fraction was obtained which had a molecular weight of 264 as determined by hydroxyl number; It was a mixture of monoand di-ethylene glycol others of the C13 OX0- alcohol, having .the formula I C13H27O-(C2H40) L4H This fraction was used to make a grease as follows:

Weight percent Polyethylene glycol ether as prepared above" 10.00 Hydrofol Acids 54 1 10.00

Glacial acetic acid 4.00 Sodium hydroxide 6.50 Phenyl alpha-naphthylamine 1.00

Naphthenic type lubricating oil distillate having a viscosity of 50 S. S. U. at 210 F 68.50 Hydrogenated fish oil acids; having a degree of unsaturation corresponding aproximately to stearic acid (commercial). Preparation-The polyethylene glycol ether, /2 of the lubricating oil and the Hydrofol acids were charged to a grease kettle and the mixture heated to 150 F. The acetic acid was added, followed immediately by a 40% aqueous solution of the sodium hydroxide. The mass in the kettle was dehydrated at 300400 F. for 1 hour and the balance of the mineral oil was added. The temperature was raised to 530-560 F. and held within this range for 90 minutes. The grease was cooled while stirring to 250 F. whereupon the phenyl alpha-naphthylamine was added. Thereafter, cooling was continued to 200 F. A portion of the grease was homogenized.

yellow product, short fiber,

Example 11 A polypropylene glycol ether of n-butyl alcohol having the formula C4H9O(C3HeO)14H and prepared by reacting ri-bu tyl alcohol with 14 mols of propylene oxide similarly as described in Example I was used for the preparation of a grease as follows:

Ingredients: 7 Weight percent Polypropylene glycol ether of n-butyl alcohol 10.00 Hydrofol Acids 54 10.00

Glacial acetic acid 4.00 Sodium hydroxide 6.50 Phenyl alpha-naphthylamine 1.00

Naphthenic type lubricating oil distillate having a viscosity of 50 S. S. U. at 210 F 68.50

Preparati0n.-The grease was prepared as described in Example I. The top fusion temperature was 570 E,-

which was maintained for minutes.

Properties Before After Homogenization Homogemzation Peiacent Free Alkalinity (as 1.63 1.63.

21 Penetrations, 77 F., mm /10: V

Unworked 419 187. Worked 60 Strokes. Semifluid 217. Worked 100,000 Strokes. 256. Dropping Point, F 500+. Witter Washing Test, Percent 0.0.

oss. Norma-Hofiman Oxidation Test, 155.

Hours to 10 p. s. 1. Drop in 0: Pressure. I I B. E. 0. Screening Test 80, 150, Excellent hear- 250 F. ing lubricant characteristics. Appearance Soft seml-fluid. Smooth,uniform short fiber product excellent.

as the lubricating oil.

Example III The polypropylene glycol ether of Example 11 was used simultaneously as a base for the great thickener and The grease was prepared as described in Example I except that the maximum temperature was 575 F. and no mineral oil was employed.

Ingredients: Weight percent Hydrofol Acids 54 10.00 Acetic acid 4.00 NaOH Polypropylene glycol of Example II 80.00

Properties Before Aitet Homogenization Homogenizatlon Dropping Point, F 474 466. Wilt-I301 Washing Test, Percent 5.

oss. Penetrations, 77 F., nun/10:

Unworked 290 238.

Worked 60 Strokes 320 280.

Worked 100,000 Strokes 350.

Norma-Hoffman Oxidation 140.

Test, Hours to 10 p. s. 1. Drop in 01 Pressure.

Appearance Dark and slightly Excellent smooth grainy. uniform product.

1 251-}4 a" diameter hole worker plate.

Example I V The mono-octyl phenyl ether of pentaethylene glycol having the formula G-(CHz-CHaOhH and prepared by reacting mono-octyl phenol with 5 mols of ethylene oxide was used for preparing a grease as follows:

Naphthenic type lubricating oil distillate hava viscosity of 50 S. S. U. at 210 F 68.50

Preparation-The alkylated phenyl glycol poly ether, /2 of the mineral oil and l-Iydrofol acids were charged to a grease kettle and heated to F. The glacial acetic acid was added followed immediately by a 40% aqueous solution of the sodium hydroxide. Heating was continued until the mass was dehydrated. ,The balance asoneva Properties Unhomog- Homogenized enized Percent Free Alkalinity as NaOH 0195 Dropping Point, F Water Washing Test, Percent Loss. Penetrations, 77 F., mm./10:

Unworked Worked 60 Strokes Worked 100,000 Strokes orma-Hoflman oxidation test, hours to s. 1. drop in 02 pressure. B. 0. Test 80, 150, 260 F Excellent lubrication-channelling type grease, no leakage through bearing seal.

Appearance Smooth uniform brown.

Example V Ingredients: Weight percent Oleic acid 10.00 C oxo glycol ether 10.00 Glycerol 2.00 Sodium hydroxide 5.00 Phenyl alpha-naphthylamine 1.00

DiOl 50 71.00

Preparation-The C10 Oxo glycol ether (256 mol wt.) was prepared by reacting C10 Oxo alcohol with 2.23 mols of ethylene oxide. The acids, ether, glycerol and /2 the mineral oil were charged to a fire heated grease kettle and heated to 150 F. The caustic as a 40% aqueous solution was then added and the mass heated to 300 F. to dehydrate. The heating schedule was as follows:

Temperature Remarks 340 Balance of mineral oil all in kettle. 435 510 566 560 560 Shut off heat. 400 Stopped agitation.

The following morning the cold grease was worked in the kettle to a smooth, uniform, slightly fibrous product.

Properties:

Percent free alkalinity as NaOH 1.48 Dropping point, F 400 Penetrations, 77 F., mm./ 10:

Unworked 341 Worked, 60 strokes 330 Worked, 100,000 strokes 375 Norma-Hoifman oxidation test, hours to 5 p. s. i. drop in Oz pressure 166 Ultimate hardness after Gaulin homogenization: Worked penetration 301 ing a primary alcohol group and an ether group having from about 10 to 50 carbon atoms per molecule, in a dispersing-proportion of a lubricating oil, heating said dispersion to a temperature within the range of about to F., adding sufficient sodium hydroxide to said heated dispersion for fusion and saponification, heating the resulting mixture to an alkali fusion-reaction temperature within therange of about 400 to 620 F. until hydrogen gas formation has receded, and then cooling the resulting grease mixture to obtain said lubricating grease wherein R is a hydrocarbon group containing from about 1 to 40 carbon atoms selected from the group consisting of alkyl and alkaryl; X is an element selected from the group consisting of oxygen and sulfur; R is a member of the group consisting of hydrogen and a CH3 group; and y is an integer from 1 to 50.

5. A process for preparing lubricating grease compositions which comprises dispersing an ether alcohol, having a primary alcohol group and an ether group having from about 10 to 50 carbon atoms per molecule, and a high molecular weight carboxylic acid having from about 12 to 22 carbon atoms per molecule, in a dispersing-proportion of a mineral lubricating oil, heating said dispersion to a temperature of about 130 to 180 F., adding a low molecular weight monocarboxylic acid to said heated dispersion followed by the addition of sodium hydroxide, said sodium hydroxide being sufficient in amount for fusion and saponification, heating the resulting mixture to a temperature within the range of about 530 to 560 F. until hydrogen gas formation has receded, then cooling the resulting grease mixture to obtain said lubricating grease composition.

6. The process of claim 5 wherein said ether alcohol is a polyethylene glycol ether obtained by reacting about 3 mols of ethylene oxide with about 1 mol of an alcohol having an average of about 13 carbon atoms, said alcohol being produced by hydrogenating the corresponding aldehyde obtained by the oxonation of an olefin with carbon monoxide and hydrogen at elevated temperatures and pressures in the presence of a group VIII metal catalyst.

7. The process of claim 5 wherein said high molecular weight carboxylic acid is hydrogenated fish oil acids and said low molecular weight carboxylic acid is acetic acid.

8. The process of claim 5 wherein said ether alcohol is a polypropylene glycol ether of n-butyl alcohol having the formula C4H9-O(C3HsO)1 iI-I 9. The process of claim 5 wherein said ether alcohol is the mono-octyl phenyl ether of pentaethylene glycol having the formula O(0H2-CH2O)6H 10. The process of claim 5 wherein said ether alcohol is a glycol ether prepared by reacting one mol of an alcohol having an average of about 13 carbon atoms with about 2.23 mols of ethylene oxide, said alcohol being produced by hydrogenating the corresponding aldehyde obtained by the oxonation of an olefin with carbon H1011! oxide and hydrogen at elevated temperatures and pres-' sures in the presence of a group VIII metal catalyst.

11. A process for manufacturing lubricating greases which comprises adding to a lubricating oil 2-30 Weight percent, based on final product, of a polypropylene glycol ether of n-butyl alcohol having the formula with a high molecular weight carboxylic acid havingfrom about 12 to 22 carbon atoms per molecule and 1-10 weight percent, based on final product, of a low mO-lecular weight monocarboxylic acid, adding sufficient sodium hydroxide to said mixture for fusion and saponification, heating the resulting mixture to a temperature within the range of about 500 to 575 F. and then cooling to obtain a lubricating grease.

References Cited in the file of this patent UNITED STATES PATENTS 2,152,137 Ricketts Dec. 5, 1939 12 Haussmann et a1 Dec. 19, 19 39 Bruson Apr. 28, 1942 Chitwood Sept. 18, 1945 i Murray et a1 Sept. 14, 1948 Morway Apr. 26, 1949 Morway et a1. Nov. 13, 1951 Morway et al Nov. 20, 1951 Smith et a1. Mar. 18, 1952 Morway et a1 Sept. 30, 1952 Morway et a1 Sept. 30, 1952 Hofer Dec. 30, 1952 FOREIGN PATENTS Great Britain Aug. 3, 1937 Great Britain 2- Aug. 9, 1938 

1. A PROCESS OF PREPARING LUBRICATING GREASE COMPOSITIONS WHICH COMPRISES DISPERSING IN ETHER ALCOHOL, HAVING ING A PRIMARY ALCOHOL GROUP AND AN ETHER GROUP HAVING FROM ABOUT 10 TO 50 CARBON ATOMS PER MOLECULE, IN A DISPERSING-PROPORTION OF A LUBRICATING OIL, HEATING SAID DISPERSION TO A TEMPERATURE WITHIN THE RANGE OF ABOUT 130* TO 180*.F., ADDING SUFFICIENT SODIUM HYDROXIDE TO SAID HEATED DISPERSION FOR FUSION AND SAPONIFICATION, HEATING THE RESULTING MIXTURE TO AN ALKALI FUSION-REACTION TEMPERATURE WITHIN THE RANGE OF ABOUT 400* TO 620* F. UNTIL HYDROGEN GAS FORMATION HAS RECEDED, ANND THEN COOLING THE RESULTING GREASE MIXTURE TO OBTAIN SAID LUBRICATING GREASE COMPOSITION. 